1,5-Cyclooctadiene

Formula: C₈H₁₂
Molecular weight: 108.1809
IUPAC Standard InChI: InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2
IUPAC Standard InChIKey: VYXHVRARDIDEHS-UHFFFAOYSA-N
CAS Registry Number: 111-78-4
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
Other names: Cycloocta-1,5-diene
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
Options:
- Switch to SI units

Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References, Notes

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	13.7 ± 0.7	kcal/mol	Ccb	Lebedev, Tsvetkova, et al., 1975	Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.049	50.	Dorofeeva O.V., 1986	The value of S(298.15 K) calculated by molecular mechanics method [ Ermer O., 1976] is about 2 J/mol*K lower than that selected here.; GT
12.76	100.
17.08	150.
21.94	200.
30.096	273.15
33.1 ± 1.4	298.15
33.277	300.
44.935	400.
55.198	500.
63.714	600.
70.722	700.
76.530	800.
81.386	900.
85.480	1000.
88.948	1100.
91.905	1200.
94.434	1300.
96.606	1400.
98.480	1500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References, Notes

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	5.8 ± 0.7	kcal/mol	Ccb	Lebedev, Tsvetkova, et al., 1975	Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1168.1 ± 0.7	kcal/mol	Ccb	Lebedev, Tsvetkova, et al., 1975	Heat of formtion values corrected; Author's hf298_liquid=7.6±0.7 kcal/mol; Corresponding Δ_fHº_liquid = 5.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	59.75	cal/mol*K	N/A	Lebedev, Lebedev, et al., 1975	DH
S°_liquid	63.17	cal/mol*K	N/A	Lebedev, Tsvetkova, et al., 1975, 2	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
47.54	298.15	Lebedev, Lebedev, et al., 1975	T = 6 to 320 K.; DH
49.74	298.15	Lebedev, Tsvetkova, et al., 1975, 2	T = 10.6 to 322.7 K. Data deposited in VINITI, No. 1324-75, 15 May 1975.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, References, Notes

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	422.7	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	422.	K	N/A	Cope and Bailey, 1948	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	203.80	K	N/A	Ott, Goates, et al., 1974	Uncertainty assigned by TRC = 0.06 K; TRC
T_fus	204.	K	N/A	Cope, Stevens, et al., 1950	Uncertainty assigned by TRC = 4. K; TRC
T_fus	201.	K	N/A	Cope, Stevens, et al., 1950	Uncertainty assigned by TRC = 4. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	203.980	K	N/A	Lebedev, Lebedev, et al., 1975, 2	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	7.89	kcal/mol	N/A	Lebedev, Tsvetkova, et al., 1975	DRB

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
11.5	194.4	Domalski and Hearing, 1996	CAL

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
-0.0939	194.3	crystaline, II	crystaline, I	Lebedev, Lebedev, et al., 1975	DH
2.349	203.983	crystaline, I	liquid	Lebedev, Lebedev, et al., 1975	DH
-0.0911	194.34	crystaline, II	crystaline, I	Lebedev, Tsvetkova, et al., 1975, 2	Irreversible exothermic transition.; DH
2.349	203.983	crystaline, I	liquid	Lebedev, Tsvetkova, et al., 1975, 2	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
11.53	203.983	crystaline, I	liquid	Lebedev, Lebedev, et al., 1975	DH
11.53	203.983	crystaline, I	liquid	Lebedev, Tsvetkova, et al., 1975, 2	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References, Notes

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

1,5-Cyclooctadiene + 2 =

By formula: C₈H₁₂ + 2H₂ = C₈H₁₆

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-55.0 ± 0.1	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase
Δ_rH°	-53.68 ± 0.02	kcal/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid

1,5-Cyclooctadiene =

By formula: C₈H₁₂ = C₈H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-4.6 ± 0.2	kcal/mol	Eqk	Taskinen and Nummelin, 1985	liquid phase

1,5-Cyclooctadiene =

By formula: C₈H₁₂ = C₈H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-0.7 ± 0.2	kcal/mol	Eqk	Taskinen and Nummelin, 1985	liquid phase

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Petrocol DH	923.	Supelco, 2012	100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1164.	Peng, Yang, et al., 1991	Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

Lebedev, Tsvetkova, et al., 1975
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, E.G.; Lebedev, N.K., Thermodynamic properties of cyclo-octa-1,5-diene, Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 1265. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Ermer O., 1976
Ermer O., Conformational interconversions of cis,cis-cyclooctadiene-1,5, J. Am. Chem. Soc., 1976, 98, 3964-3970. [all data]

Lebedev, Lebedev, et al., 1975
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, Y.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane and 1,5-cyclooctadiene, Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]

Lebedev, Tsvetkova, et al., 1975, 2
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, Y.G.; Lebedev, N.K., Thermodynamic properties of cycloocta-1,5-diene, Zhur. Fiz. Khim., 1975, 49, 2152. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Cope and Bailey, 1948
Cope, A.C.; Bailey, W.J., Cyclic Polyolefins II. Synthesis of Cyclooctatetraene from Chloroprene, J. Am. Chem. Soc., 1948, 70, 2305. [all data]

Ott, Goates, et al., 1974
Ott, J.B.; Goates, J.R.; Reeder, J., Solid + liquid phase equilibria and solid-compound formation in hexafluorobenzene + cyclic hydrocarbons containing one or two pi-bonds, J. Chem. Thermodyn., 1974, 6, 281-5. [all data]

Cope, Stevens, et al., 1950
Cope, A.C.; Stevens, C.L.; Hochstein, F.A., Cyclic Polyolefins V. Preparation of Bromocyclooctadiens and 1,3,5-Cyclooctatriene from 1,5-Cycloctadiene, J. Am. Chem. Soc., 1950, 72, 2510-4. [all data]

Lebedev, Lebedev, et al., 1975, 2
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, E.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of Methlenecyclobutane and 1,5-Cyclooctadiene in II, Thermophysique, Quatrieme Confirence International de Thermodynamique Chimique, pp 20-8, 1975. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]

Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G., Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes, J. Am. Chem. Soc., 1973, 95, 8605-8610. [all data]

Taskinen and Nummelin, 1985
Taskinen, E.; Nummelin, K., Relative thermodynamic stabilities of the isomeric cyclooctadienes, Acta Chem. Scand., Ser. B, 1985, 39, 791-792. [all data]

Supelco, 2012
Supelco, CatalogNo. 24160-U, Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusS	Entropy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.